Scary first hires, outsourcing laundry, and reality shows we’d go on: Conversations with Sisters

When you make it to the point where you need to hire your first employees, you’ve achieved a significant milestone in your business – one that can be completely terrifying. Courtney and Dana talk about their experience. Plus, when is it the right time to ask for help, even for the little things like folding socks? And what reality TV show would you want to go on?

If you haven’t listened to last week’s episode with Sugar Euphoria‘s Randi Smith, check it out on Apple Podcasts, Spotify, or any other podcast app.


Dana: It’s hard to be on the outside of an entrepreneur. It’s hard to look at someone’s life. And entrepreneur’s life and not judge it harshly because either they work too much, they work too hard. It’s not worth it, or it’s frivolous.

Like there it’s, cause it’s, it’s hard to understand the ins and outs of it. 

Courtney: Welcome to Hustle and Gather, a podcast about inspiring the everyday entrepreneur to take the leap. I’m Courtney, 

Dana: and I’m Dana,

Courtney: and we’re two sisters who love business. On this show, we talk about the ups and downs with the hustle and the reward at the end of the journey 

Dana: And we know all the challenges that come with starting a business. Between operating our wedding venue, doing speaking and consulting, and starting our luxury wedding planning company, we wake up and hustle every day.

Courtney: And today we’re talking, just the two of us, about last week’s episode with Randi Smith, founder and lead designer of Sugar Euphoria, a boutique wedding cake and confectionary studio in North Carolina. If you haven’t heard last week’s episode, go give it a listen and come back to hear our thoughts.

Dana: All right, court, let’s get started. 

Courtney: Let’s get started. All right. Well, I thought that was a great episode. One, I love Randi. It’s like always so fun to talk to a friend. 

Dana: It is 

Courtney: We’ve known Randi since she started. 

Dana: I know, but what I, I love how calm she is. Like she’s such a calming presence, like I want to have like a cup of tea with her and like cuddle up in like a, 

Courtney: not a Bahama mama?

Dana: I’ll have that too, that’s fine. 

Courtney: No, I feel like, I feel like that’s the Caribbean in her. Like, I feel like she is like on like her own schedule a lot of time, then she said always just seems non-phased, even when she should be like freaking out, she never is. 

But great, it was a great episode. It was really enjoyed it, but it started off fun. I loved how she was talking about Netflix, that clearly, we’re going to be on together as the sugar rush. what Netflix show would you want to be on or what net Netflix show would you create to be on? Like would be like one that would fit you? 

Dana: That is so hard. I like, I don’t think I’ve ever watched like a reality TV show and was like, I should be on there, like legitimately. 

Courtney: I mean, but really like how much reality TV have we even watched? 

Dana: I mean, I’ve gotten into the bachelor and bachelorette to like, you know, be cool, like the girls in our office.

Courtney: Fun fact. I’ve literally never seen an episode of the bachelor. 

Dana: Well, I was in college and the very first one aired and we all watched it religiously. 

Courtney: Really?

Dana: We were huge Trista fans; very upset he did not pick her. that was the person who he dumped, and then she became the first bachelorette and she married Ryan and whatever, anyways, oh, I don’t know. I mean, I, I feel like it would just be interesting to have a Netflix life about like this entrepreneur life, like just the life of what it is, all the ridiculous shit that we had to do all the time. 

Courtney: So ‘the life of what it is, the entrepreneurial life’ You’re probably not going to be in a think tank for Netflix anytime soon.

Dana: We all know, that’s not my strong suit. Now, what would yours be? I can tell you thought about this. 

Courtney: I haven’t thought about it. I really haven’t thought about it. Well, like when I was, it was a TLC show. I always thought it would have been so much fun to be on Trading Spaces. 

Dana: I knew you were going to say that.

Courtney: Oh really? I loved that show growing up and now I would never want that. I would hate for someone to come into my space and trade it, I would be pissed. 

Dana: Yeah, cause they probably do a terrible job. 

Courtney: I feel that way.

Dana: What if we switched places? I did your house, you did mine. 

Courtney: Well, I felt like that could probably end up better, cause you know like the standard or like what my vision would be. 

But I think our Netflix show would be something more along the lines of like the messiness of being sister-preneurs. Like it have to be something like ‘ sister-preneur: behind the smile’. 

Dana: It’d be a lot of drama, 

Courtney: something like that. I don’t know. But it would have to be real like, and how real are those people? You know what I mean? 

Dana: I don’t know. I think there is some realness to it, but like I said, I think they edit it to what, they find the villain. They have to have a bad guy, a good guy. 

Courtney: Obviously you’d be the bad guy. So I don’t know, maybe you wouldn’t be on this Netflix show. 

Dana: I’m just the silent partner, my face would be blurred out. I do not agree to be videotaped. 

Courtney: So I think something along those lines, but think it’d be fun. 

Dana: So I, I thought she just had like a ton of great tidbits, but when she was telling the story about how she did her first one-on-one class and she, they told her how to properly roll out fondant, and at the end, she was like, and here’s how I do it. Like basically the shortcut way to it. She was like, what is like what I need, but it made me really think that there’s always something in business that you had to do the hard way first before you can learn the easy way. 

Courtney: Like something specifically related to business that we had to do?

Dana: Of life, I guess life is fine. It doesn’t have to be business, can be life. 

Courtney: I don’t know. Sometimes I feel like I’m still learning things the hard way. Yeah, like I haven’t figured out the easy way. Kind of like math, when I thought about that, it made me think of like trigonometry and how you had to like, learn like all the like trigonomic functions before you could just actually put them in your calculator.

That’s what it made me think of, had to learn that the hard way before figuring out the easy way. But maybe if you say something it’ll inspire me to think of something. What was your hard way? 

Dana: The thing I, I honestly thought it’s just like learning how to like manage people, like learning how to figure out how to communicate with your employees in a way that’s effective.

And I think that the hard way is still always, still works great, but to me, it’s, it’s trying to figure out like, like what makes them tick, who they are. And you can take, to me it used to be like, oh, we’re going to spend so much time with each employee, we’re going to like, invest this, like every Wednesday and have lunch together.

And you like actively try to seek out to connect to these employees. And I’m not saying I don’t that anymore, but now it’s just more of, okay. Like, let’s take your enneagram test, let’s figure out what makes you tick, let’s figure out what color you are, and like I can automatically like, kind of, it’s a little bit more, not as much of a shot in the dark, but like, I know you’re going to love this or whatever.

Do you know what I mean? Like kind of creating, using tools to figure out how’s the best way to communicate instead of trying to figure it out. That makes sense? 

Courtney: I think that’s definitely true. I, that made me think of how we’ve been talking about how to find the employee to fit your job as opposed to creating a job around an employee. And I feel like we danced around that tree a couple of times. 

Dana: And we still do. And we have to say no, no, no, no. Let’s go back to like our core truth. I know this morning we had this conversation, let’s go back to our core truth that we do not need to create a job to fit this employee. This employee is our employee right now, and it fits the job now.

But if this job evolves because what we need it’s okay, and maybe it’s not the right employee for that job. 

Courtney: Yeah. Which sounds like, so like gut wrenching, you think about that, but then it’s not a business decision. It becomes a personal decision right, where you’re like, well, maybe that person doesn’t fit. 

Dana: And then it becomes a business disaster.

Courtney: That’s right, yes. And then it becomes very personal, this is disasters feels so personal. But I think maybe that like, going through that the hard way a couple of times and then realizing, all right. It’s, it’s really, it’s just business. It’s not personal. And you’ve got to do what makes sense for your business and for everyone else around you.

Because I think sometimes you make decisions for one person, right, and instead of just making the hard decision about that one person you’ve now affected like the other eight people in your office, for trying to like preserve one person. I think that’s super hard. 

Dana: I agree that.

Courtney: Another thing I love that she talked about, and I feel like you could talk more about this than I could, because I think there’s really nothing in my business that I wouldn’t be okay turning over to somebody. Well, that’s actually not true, probably big overarching financial things I wouldn’t want to turn over, but everything else I’m cool. But what’s that one part of your business that you don’t want to turn over? 

Dana: That’s hard. 

Courtney: Yeah. The one thing. She said it was take deliveries, right? She would do all of this and she does, she wants to deliver it.

Dana: I feel like mine isn’t like concrete either. And to be fair, this idea that you couldn’t give up finances is new. Because when we first started, you didn’t really even care about overarching finances really, it was just, you know. 

Courtney: No, to be clear, I do not want to be in the day to day. Like, I don’t care about like paying a bill or anything like that. If we’ve made a decision to hire this person and its X number of dollars, but like where’s our money going long term kind of thing. 

Dana: I feel like we should never give that up. 

Courtney: I’m just saying that’s the only thing

Dana: For me, my control is time. That’s my control, like and that sounds very weird, but I don’t think I could ever give up having a non-nine to five office or a nine to three, whatever office hours are like I do not like solely like, Remote offices. Like, I like to see my people. I like to know that if I’m going to like randomly stop by the office and I’m going to see at least two faces there.

Because I didn’t feel that way for many years. Like if we were gone for a week, I wasn’t certain that people actually showed up at the office. 

Courtney: They probably didn’t. 

Dana: Yeah. And I don’t know why, they could be more productive at home, but it’s something about seeing them there, like someone having their eyes on everything. Like, I don’t know.

Courtney: Potentially, this kind of like a catch 22, like I might make different decisions, we might make different decisions about our schedule that might even be more beneficial if we weren’t feeling like we were answering to other people in the office.

Dana: Oh, I have, I have let go of that a little bit. Like where I can look at it and say, like, if I know I’m done for the day and like, like couple weeks goes because internet was making me angry. I was like, I can’t do anything here. I’m just going to go home work from home. or if I’m like, hey, I got my stuff done,

I’m going to work from home on Friday mornings. That’s fine. I don’t have any qualms with that because I know I’m going to get my shit done, right. Like, but I like to see everybody else, even though I should trust them and they all are great people, but I don’t think I’ll ever give up, like, just being like, just come in whenever you want. Yeah, I want to know a schedule, like give me your schedule and please commit to it. 

Courtney: Being a venue, with people coming in and out all the time and vendors coming in and out, you have to have somebody on site.

Dana: I know, but we used to just be like, oh, you worked this weekend. So you don’t have to come in Tuesday until 2:00 PM. And it was just like, no, no, no, no, no, no, no. Like I give you enough vacation time. Just take the morning, tell me you’re not going to come in and take your vacation time for it. But you, if not, then show up at 9:00 AM. Not 9:10, not 9:30, but 9:00 AM. 

Courtney: So control of other people, the one thing that you’re going to turn over is controlling other people? 

Dana: That is true. 

Courtney: Just to be clear. But I, one of the things though that it really made me think of is how Randi is kind of in this perpetual, like solo-preneur thing, right? Like she it’s like, you know, interns and we have interns too, but they’re like, it’s fleeting. Like you had an intern for four months and then you’ve got a lull and another intern that you’re training. So you’re constantly training and retraining, and while it can be helpful for business, there’s a lot of time that’s committed to getting an intern to where they’re useful to you.

But I thought it was really interesting about it’s almost, like she doesn’t want to take that risk cause she doesn’t want to give up the control of it. 

Dana: And I wish we had asked that to kind of dig a little deeper into that. But no, I agree, but I think there is a lot of fear with hiring. There’s a lot of fear and of, you know, can I guarantee their paycheck? There’s fear of, are they going to learn all my secrets and open up their own thing? There’s fear of them being more work in all actuality for you. Like maybe it’s not going to take the load off is just going to add a different kind of load, whether it’s like a pressure or whether it’s just now I have to manage this person.

Because that is a thing, I don’t think we fully understood where like, we’re going to hire these people, take this off our plate and it’s going to be great, we’ll have all the time. Well, no, the time is just spent doing something different and half that is, maybe I have half my time back, cause the other half time back is managing them and making sure they’re doing their job, right? 

So it’s not just like a one for one, like you hire this person and now you have all this time. It’s like, I have some time back, like I just got a little bit back, you know? So I think there’s a lot of fear with that. And, you know, and I think for us that we have found is every time we have grown, it has only like pushed ourselves to more than we could have imagined. Like the business is flourishing because of it, whereas if we had just stayed the two of us, 

Courtney: well, you would only be able to take on so many events, right? You’d have to limit what you could do. So you can only grow so big as a solo preneur or for us, like as a duo which is functioning as a solo-preneur. 

Dana: Right, but it was just interesting because a lot of people will make the argument, well they that’s fine. Like they just want to take a certain amount of events and they want to charge what they want to charge, but I honestly think that there’s a point when you, when you tap out of a market, like when you tap out of it, like you’re saying, okay, I only want to do, I’m going to say I’m a solo-preneur and only do 10 weddings and, or 10 whatever.

And I’m going to charge, you know, 5,000, $10,000 a cake I’m going to be great, right? The ability to get that $10,000 client is going to dwindle and dwindle and dwindle, like so much more because you’re going to have new competition and all this stuff. And so to me, and we’ve talked about this often is creating a diverse marketing plan where you’re hitting that ideal client X amount of times a year, but you also have your bread-and-butter client who’s paying the bills at the end of the day. 

Courtney: And giving you exposure, like they’re keeping your name out there because if you’re name’s only going out into the free world, like 3, 4, 5 times a year, right. Who’s going to know about you?

Dana: That’s been like our biggest fear with the collective is our girls are becoming like such stronger, stronger planners that like they can do so much more.

Courtney: And they want to do so much more. 

Dana: We’ve had the conversation about like, do you just get rid of event management? And I was like, no, like you don’t get rid of it because it’s what exposes us to so many venues, and so many things that once you take that 25% of your business out, like we’re no longer on Instagram feeds and whatever. And when people search for this venue, and you’re not in a recent Instagram feed in the next six months or six months, they’re not going to book you.

Courtney: It’s kind of like the net. To catch that big one, you have to like, get all the little fish before you get the big one. You know what I mean? But you’re net, it has to be out there. Yeah, so I think, I think scaling like with team members helps you do that. 

Dana: Because it helps you manage those little things. So you can, so you can do the big things that you want to do, and get to that level.

Courtney: And I think too, like one of the things about hiring a team and growing in that way. And yes, it is scary, like our first hire was super scary. I remember like we’re going to commit to paying somebody else $30,000 a year? We don’t even pay ourselves $30,000 a year. 

Like it was super scary at the time, but it allows for you really to… One of my favorite books growing up was Anna of Green Gables, and she always talked about her scope of imagination, like when she got to green Gables, I just provided so much scope for imagination. And I feel like when you hire a team, it allows you to get back into that space where you have some scope for imagination. Now don’t get me wrong, it’s not like you’re dreaming all the time because you’re certainly in the trenches.

Sometimes you have to pinch hit. You are doing training; you’re dealing with office dynamics or whatever it is. There’s certainly those things, but I think by and large, it allows you to take like a top-down, picture of what’s going on in your company, because you can step away on some level. And it also allows you to pursue other things that might peak your interest and your passion.

And I think that we’ve noticed that, you know, we had C&D Events, it was you and I. We hired on Becca. We had interns that became planners, like Kelsey was during that time. We opened the Bradford; we have Hustle and Gather. All of these things have each fueled, the thing that came before it and made it even bigger.

So being able to kind of project and being able to like open your mind to what’s coming next allows you to really grow what you had before, right? So I think it allows for that. 

Dana: Yeah. I think that’s very true. 

Courtney: Yeah. Yeah. It’s a scope for imagination. We’re not imagining anything right now, though. We’re not, we’re done imagining tapped out, tapped out no more.

Dana: Imagine that I am at my max. 

Dana: Oh. So I really love to like kind of segue. Not even, that’s not even a great segue, but just moving into the next, I thought was a good meat in the heart of her interview was asking for help. I loved her comment on her mother-in-law who said, yeah, I’ll sort your socks. And I was just like this like guttural reaction of like there’s a lot of times you get to the, the laundry and you’re like, I don’t want to do this and you just throw it in the unmatched bin. And then eventually they get you, you can’t find socks for everything. Like, hey, we got to match the socks.

And it’s like such a labor of love for someone to say, I’m going to sort your socks for you. And you’re like, that would, I don’t know. 

Courtney: What would be your sort your socks thing?

Dana: Honestly, probably anything with meals, like meal planning. Like if someone would like plan my meals for me, like, I, I it’s, it’s my least favorite thing to do. I know I do it. 

Courtney: You do it quite thoroughly. 

Dana: I know, but I hate it every time. I’m like, ugh, I got to get this done. I got to figure this out. But I find it to me, and it’s probably why I do this for people, is when anyone’s having a hard time, I just want to bring them food because I think it’s the one thing that is the most stressful to think of.

Especially when you have children and like, whatever’s going on and you’re like dinner, like what are we going to do for dinner? How are we going to get there? Like whatever, and I felt this a couple like, this is like a couple weeks ago. I got back from Vegas and had a procedure done a couple weeks ago. I guess it was 10 days before Vegas. It was supposed to be a one-day recovery, it was not. Like a three-week recovery, it’s been very traumatic. 

But anyways, I felt awful and I was on this antibiotic and made me like super nauseous and like I was dizzy and like, it was terrible. And like, and I had a meal plan. Oh, I didn’t, I didn’t know. Plan. When I got back from Vegas, I didn’t have a meal plan and Sam, I remember, I was like, we didn’t hear it. I’m like, I don’t, I just don’t care. Like I just don’t care. Like just whatever fix it, make it it’s, you know, and it, and it wasn’t stressful, but it was stressful to me, I was like, you know, do we even have stuff to make food or whatever?

And I remember like, he, all this is going down. And like, I went to the doctor, the follow and they told me what was going on. And I call him and I was like in tears, and I was like, I’m on the edge, like, I’m on the verge, like, I don’t think I’m going to, like, you need to pull me back. Like, this is too emotionally hard.

And he was helping his brother move, and I know his whole family was there. His whole family heard that conversation, and like, nobody was like, hey, like, do you need help this week? Or, yeah. Do you know what I mean? And I was like, I don’t ever want to be that person. I’ll never hear it, like tears in someone and not say, hey, what can I do for you? Yeah, let me be there for you. Do you know what I mean?

Courtney: But flipping it on its other side, you should have said, can you ask your family to bring us a meal? Like I just can’t handle it, and it’s like putting me in like a mental, right, could have asked your sister, and I would have brought you a Costco pizza, but still it would have been something. 

Dana: Right. No, I know, and I, that is my problem. Is I just, 

Courtney: so it is pride? 

Dana: I don’t think it’s pride or I think it’s ego. I think it’s the wrong expectation of people. 

Courtney: Like an unspoken expectation of other people. That will get you in trouble, 

Dana: They will, because it’s not how I would behave. You know? 

Courtney: You should see Dana’s meal plans. No, one’s going to behave like that. So, no, one’s taken that off your plate. Maybe you just need to meet, like, this is what I do. So I’m like, all right. I know myself at this point, right. I’ve cause I’ve been around almost 40 years, right? I know I’m not going to cook dinner every night. Like I know that there’s going to be a handful of nights that I just need to be able to shove something in a microwave or put something in the oven and cook, or tell Mason to do it, right. 

So I’m like, realistically, I’m going to cook maybe three nights a week, like that’s realistic. One nights going to be leftovers. So night we’re going to go out. So I get the things that I think are like the healthiest, right? Like, I’ll get like the Tiki masala already pre-made at Costco. I will buy the rice that you just put in the microwave that’s in the bag, even though it’s sacrilegious and crazy expensive, but it’s 90 seconds in that, in the microwave.

And my dinner is literally done, right. And cause I just know that’s what I can handle. Throw in some steam bag vegetables. I’m not cleaning anything up. Everyone’s eating healthy food and it’s done. So I think just like wrapping your mind around, it’s a little bit more expensive for sure, right? Like the Tiki masala, and rice not in bags is cheaper, but at that point I don’t care. Like I don’t give a shit, like everyone’s fed it’s off my plate and I know it’s what I can handle, but I think sometimes maybe you just have too high of an expectation of yourself. 

Dana: Yeah, no, I do. I, that is true, but like, I don’t begrudge cooking dinner. I don’t mind it. 

Courtney: It’s the planning. 

Dana: It’s the planning. I can, if there’s not a meal plan, I will not cook. I will not do it because I will not scrounge to the pantry and try to figure it out, cause it just frustrates the hell out of me. So ask, what do you want? What you want? I don’t care. I don’t care. I’m like, well then obviously eat some cereal because that’s what I’m eating. Yeah. Like that’s what we’re having. 

Courtney: Some things in the freezer that you just like or the whatever.

Dana: I know that. I’m just saying, like, I think it’s one of those things where I still am learning even as old as I am. Even going through all the, even having babies and all these things, like saying, I do need, it’s something that I need help, because need is a very strong word. I would like you to care enough to help me.

Courtney: I would like for you to care; I’d like for you to give a shit and help me. 

Dana: Yes. Please recognize this. That like, this is hard.

Courtney: Absolutely. But I don’t know what my sort, my socks is. 

Dana: Clean your house. 

Courtney: I do, I I but that, I mean, that’s an easy fix, but the thing that I don’t like about cleaning my house is it has to be all picked up and ready.

And like, most of the time, like the downstairs in my house is, but my kids’ rooms, I think it would be like, totally like cleaning my kids’ rooms, like cleaning the top floor of my house. Like organizing it, getting it to where it’s manageable. Yeah. So it would be like, it would be my sorting my socks. 

Like my kids’ stuff in particular. Yeah. And it’s hard too, cause like we’re building a house and going to move and within sometime in the next year. So like how much effort and energy do you put into it? And yet it still bothers me. You know what I mean? Like I remember when you guys were getting ready to move into your house, you like stocked your house with whatever it is that you were purchasing for your new house.

Like you even like closed off one of the bathrooms because it was full of boxes. And I was like, you’re one norovirus away from like disaster because you have one toilet for you four people, but whatever. That stresses me out, like all of those, like in-process thing. Like I couldn’t live, like I couldn’t live like that because I can’t relax. 

Dana: I do love that, but clutter, if I know there’s an end in sight, it doesn’t bother me. 

Courtney: It bothers me. 

Dana: Like I just, I like, literally don’t look at it during the week and Saturday morning, it’s like, we’re going to pick it all up. And the kids know, like there’s certain things they should do but I just, I just, I don’t have the energy to worry about it or to care about it. So I just ignore it. I know it’s just fleeting. 

Courtney: Yeah. I mean, we’re not perfect over there for like, there’s definitely times. 

Dana: But your house is always picked up. 

Courtney: But my kids know, because they know like, they’re like, she’s about to go bat shit. You better pick that up. And Mikael knows, like this is really going to bother her. So he makes it happen. 

Dana: Yeah. So the other thing I loved when she was giving advice was, Like, you’re going to give yourself all the reasons why you shouldn’t do it and they’ll never be right. So, and we’ve heard this over and over again with people on the podcast, like, just do it. You can always talk yourself out of it.

But what was some of the, like, what did you try to talk yourself out of when we started? Like, what were some of those things that you were saying that I shouldn’t do this because… 

Courtney: Well, I felt like with like C&D I didn’t have any of that cause it was just, it was low risk. Right. It kind of started like, as a, jobby like from the previous episode with Megan. It’s a job hobby. So it was just fun, low risk something to try and plus we were like super young at this time. So like all the energy, all the energy, right. All the time. 

But definitely with the Bradford, I mean, I definitely had a fear that it was never going to be good enough. Like we were never going to have the space that I would deem good enough that it wasn’t going to be successful enough that I thought, for sure, like, we’d be working the weddings or doing sales, or like, I didn’t imagine the team that we would have. And so I felt like that would become a lot. Definitely some of those worries. 

Dana: Yeah. I think mine are pretty similar. I think C&D I didn’t have, like you said, probably as much stress about it. I think there came a point when we were getting really busy and I was just like, it was that kind of like shit or get off the pot point, you know, like either you’re going to do this or we’re just not going to do it. And I was really afraid to really want it. I was always so fearful. I think it was time. Like it was going to like absorb so much time and I was going to regret, like not being home or not, you know, 

Courtney: Which she talked a lot about that. Like she talked a lot about how, who did you disappoint?

Like whose perception did you let down their, like their perception of you by opening up your business? Right? Like, there’s always going to be someone like, if it’s like a spouse or a mother or your kids or whatever you remember, she was talking about that, and I’ve never had a whole lot of guilt concerning that because I feel like there is equal benefit to my children to see somebody like pursuing something that they believe in passionately as much as, you know, being the 365 moms, you know what I mean?

Dana: But you have actually a very similar story to hers, like you, you went to premed, you were supposed to go to med school and you made the decision you didn’t, and everyone in your life at the time would have told you that you just didn’t do it because like, I honestly thought you didn’t do it because you were depressed and like, in this period of like, almost laziness, like it’s just like, it was going to be too hard.

Courtney: Thank you for that mental health. Like I was in a period of depression. You just equated it to laziness.

Dana: At the time we didn’t know you were depressed. I know now that you were, but like, I just thought like, oh, she’s just settled.

Like she just decided it was like, and it wasn’t until years later, when I think we had a real conversation, you’re like, I just didn’t want it, wasn’t what I wanted to do. But for so much of your life, you told everyone you were going to be a doctor from the time you were like five or six. Just like from the time I was five first day kindergarten, I was like, I want to be a teacher.

Yeah. And I think we were allowed to change our opinion, but I felt like it, it was so much of who we were as kids, like deciding this path that and I only, I taught and then I’ve fulfilled that, what I said I was going to do. And then I did this where I feel like you took different, like a little bit of a windy path from like med school to selling insurance, to teaching to here, you know?

And so I think you’re you, I think you have a little bit more of an ease of like starting new things and realizing, hey, this isn’t what I wanted. This is what I want to do because you know, you’ve done it. He’d done it a couple of times. You know, I had a little bit of a hard time with it, giving up on that, what I thought I was going to be. And it wasn’t even like, we were like, oh, the money was terrible. I was like, yeah, the money was terrible. It wasn’t why I quit like. 

Courtney: Teaching.? Yeah, because definitely owning our business. That money was terrible for a whole lot longer. 

Dana: It was, but it was very much like, I honestly thought I was going to like change lives. Like I was going to change the world, teaching these children. And I realized I was not going to do that. 

Courtney: Change your own life, you had become very jaded. 

Dana: You know? And so there was just a lot of that. I don’t know if I disappointed anybody. I, I mean, I could probably maybe assume, but I don’t. No one’s ever told me that they were disappointed.

Courtney: I felt like for us, like when we started the business, it was always like their little thing. You know what I’m saying? I remember even like your in-laws talking about it. I remember like our family talking about it and it was just, oh, they’re, you know, they’re doing a little thing, 

Dana: Like we’re selling something online.

Courtney: Like we were like a multi-level marketing, like we were selling Mary Kay, right? And I was like, no, no, no. Like, I don’t, it’s not that, like, it’s just not that. So I felt like somewhere underneath there was something to prove to me like that, that I had that, that was like a changing people’s perception in that way.

Like you are undervaluing what I’m doing or you’re underestimating what this thing is, this isn’t a multi-level marketing scheme. 

Dana: No, I agree. I don’t, I don’t know. I don’t know my in-laws think of it to be truthful with you. I don’t think they are; I don’t think they’re disappointed, but I mean, I was a science major, which is what they were, and I think that was always like, they could relate to me on that level. And then like now they don’t, I guess. I don’t know. 

I think it’s; I think it’s hard. It’s hard to be on the outside of an entrepreneur. It’s hard to look at someone’s life. And entrepreneur’s life and not judge it harshly because either they work too much, they work too hard. It’s not worth it, or it’s frivolous. Like there it’s, cause it’s, it’s hard to understand the ins and outs of it. I think sometimes when you look at, and I’d say it’s a lot about Sam, like he’s, he does a ton of stuff, but I think it’s a lot of people it’s like, maybe he does too much. Like maybe I’m not enough of a mom. 

Like maybe I don’t, maybe I put the brunt of the work on him too much because like chasing this dream quote unquote or whatever. And I’m like, no, I’m like trying to pay for our retirement over here. Like I’m trying to give us a life that we want, you know? And as, as, as he, I mean, he works just as hard at his job, you know, it’s just different. Yeah. 

Courtney: Like the confines of certain hours, which is helpful.

Dana: Right. Where entrepreneurship, it’s not boundaried. There isn’t as many boundaries and being entrepreneurial. We not can’t, you can’t draw those lines in the sand. 

Courtney: You can’t like really speak into anyone else’s like family dynamic really, right, what works for them may not be what works for you. You know, like I feel like even her talking about her husband.

And I think about other cake businesses where I’m like, wow, like I think of a couple of creative people whose husbands literally quit their job to support what their partner was doing, and then that’s not our story. She sounds like she’s in a business in a household of two entrepreneurs which I think looks very, very different, very different. Yeah. Very down pressures. 

Dana: I agree with that. I definitely think it’s and I mean; I still judge people all the time. Like, what is that? Why is that family operate that way? That seems weird. Like it’s normal, it’s not like, it’s a normal thing to look at an outside and be like, I don’t understand how that works, but I think that’s where you have to take a step back and say, I don’t understand how that works.

Yeah. Therefore I can’t make any pass judgment on it, you know? 

Courtney: Yeah, absolutely. Well, cheers to not using your degree. Oh yeah. I know. Sorry, mom, dad. 

Thanks everyone for gathering with us today to talk about the hustle. For our episode with Randi, we picked a Bahama mama cocktail, and we hope you’ll get the chance to make it this week. And cheers again to those who will sort your socks.

Dana: And to learn more about our hustles visit,, and our newest one Or follow us on Instagram at canddevents, at thebradfordnc, at hustleandgather, and at And if you liked the show, be sure to subscribe and leave us a rating and a review.

Courtney: This product is a production of Earfluence. I’m Courtney.

Dana: And I’m Dana.

Courtney: And we’ll talk with you next time on Hustle + Gather.

Full Episode Transcript

Hustle and Gather is hosted by Courtney Hopper and Dana Kadwell, and is produced by Earfluence.  Courtney and Dana’s hustles include C&D Events, Hustle and Gather, and The Bradford Wedding Venue.

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